A Novel Recyclable Organocatalytic System for the Highly Asymmetric Michael Addition of Aldehydes to Nitroolefins in Water

Dhruba Sarkar, Ramesh Bhattarai, Allan D. Headley*, Bukuo Ni*

*Department of Chemistry, Texas A & M University-Commerce, Commerce, Texas 75429-3011, USA, Email: allan_headleytamu-commerce.edu, bukuo_nitamu-commerce.edu

D. Sarkar, R. Bhattarai, A. D. Headley, B. Ni, Synthesis, 2011, 1993-1997.

DOI: 10.1055/s-0030-1260465

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Abstract

A strategy for the asymmetric Michael addition of aldehydes to nitroolefins with a catalytic system of an organocatalyst in combination with ionic-liquid-supported benzoic acid gives excellent diastereo- and enantioselectivities. A notable feature of this organocatalytic system is that the catalyst can be recycled more than 12 times without significant loss of enantioselectivity.

see article for more examples

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Diarylprolinol Silyl Ether Salts as New, Efficient, Water-Soluble, and Recyclable Organocatalysts for the Asymmetric Michael Addition on Water

Z. Zheng, B. L. Perksin, B. Ni, J. Am. Chem. Soc., 2010, 132, 50-51.

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Key Words

aldehydes, asymmetric catalysis, green chemistry, ionic liquids, Michael addition, Nitro Compounds

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ID: J66-Y2011-1790